Basic information
- CAS
4969-02-2- Standard SMILES
CN1CCCC(CC2c3ccccc3Sc3ccccc32)C1- InChIKey
MJFJKKXQDNNUJF-UHFFFAOYSA-N- Molecular formula
- C20H23NS
- Average molar mass
- 309.5 g/mol
- Monoisotopic mass
- 309.15512091
Overview
Metixene is a member of piperidines and a member of thioxanthenes. It has a role as a histamine antagonist, an antiparkinson drug and a muscarinic antagonist.
Names & identifiers
- Preferred name
- Metixene
- IUPAC
- 1-methyl-3-(9H-thioxanthen-9-ylmethyl)piperidine
- English name
- metixene
- Molecular formula
- C20H23NS
- Molecular weight
- 309.47
Names & synonyms
MetixeneMETHIXENETremaril4969-02-2Methixart1-Methyl-3-(9H-thioxanthen-9-ylmethyl)piperidineMethixenMetixenoMetiseneMetixenum32VY6L26ZWDTXSID1047867
Show more names
TrestTremonil60 SJ 1977Aids-001633metixene USP/EP/BP60 Sj 1977 (*hydrochloride*)9H-Thioxanthene, piperidine deriv.
CHEBI:51024RefChem:818765DTXCID1027843N04AA03225-610-6AtosilMethixen [German]Metisene [DCIT]
Database identifiers
- CAS
4969-02-2- PubChem CID
- 4167
- DTXSID
DTXSID1047867- ChEMBL
CHEMBL1201342- ChEBI
CHEBI:51024- UNII
- 32VY6L26ZW
- EC Number
- 225-610-6
- Nikkaji
- J8.790D
Properties
Computed structural properties
- XLogP
- 4.9
- Topological polar surface area
- 28.5 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 2
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 349
Experimental & physicochemical properties
DrugsPharmaceuticals
LogP4.7
Solubility
Soluble as HCl salt
1.02e-04 g/L
Melting Point
< 25 °C
< 25 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 25 °C · <25 °C
- Boiling point
- 0.07 · bp0.07 171-175°
- Density
- 1.118 · 1.118±0.06 g/cm3(Predicted)
- pka
- 9.46 · 9.46±0.10(Predicted)
- FDA UNII
- 32 VY6L26ZW · 32VY6L26ZW
- NIST Chemistry Reference
- 1 · Piperidine, 1-methyl-3-(9h-thioxanthen-9-ylmethyl)-(4969-02-2)
- Symbol(GHS)
- 7 · GHS07,GHS09
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxicology
Exposure RoutesAbsorbed in the gastrointestinal tract following oral administration, however the extent of absorption is not known.
Toxicity Summary
Parkinsonism is thought to result from an imbalance between the excitatory (cholinergic) and inhibitory (dopaminergic) systems in the corpus striatum. The mechanism of action of centrally active anticholinergic drugs such as metixene is considered to relate to competitive antagonism of acetylcholine at muscarinic receptors in the corpus striatum, which then restores the balance.
Signs and Symptoms
Signs of overdose include dilated and sluggish pupils, warm, dry skin, facial flushing, decreased secretions of the mouth, pharynx, nose, and bronchi, foul-smelling breath, elevated temperature, tachycardia, cardiac arrhythmias, decreased bowel sounds, urinary retention, delirium, disorientation, anxiety, hallucinations, illusions, confusion, incoherence, agitation, hyperactivity, ataxia, loss of memory, paranoia, combativeness, and seizures.
Carcinogen Classification
Chemistry & industry
Pharmacology
ATC Code
N - Nervous system
QN - Nervous system
Pharmacodynamics
Metixene is a tertiary antimuscarinic with actions similar to those of atropine; it also has antihistaminic and direct antispasmodic properties. It is used for the symptomatic treatment of parkinsonism, including the alleviation of the extrapyramidal syndrome induced by other drugs such as phenothiazines, but, like other antimuscarinics, it is of no value against tardive dyskinesias. Metixene has been discontinued.
Mechanism of Action
Parkinsonism is thought to result from an imbalance between the excitatory (cholinergic) and inhibitory (dopaminergic) systems in the corpus striatum. The mechanism of action of centrally active anticholinergic drugs such as metixene is considered to relate to competitive antagonism of acetylcholine at muscarinic receptors in the corpus striatum, which then restores the balance.
Metabolism/Metabolites
Hepatic. Metabolism occurs via sulfoxydation and N-demethylation.
Hepatic. Metabolism occurs via sulfoxydation and N-demethylation.
Absorption, Distribution and ExcretionAbsorbed in the gastrointestinal tract following oral administration, however the extent of absorption is not known.
Cellular LocationsMembrane
Uses & manufacturing
UsesUsed for the symptomatic treatment of parkinsonism.
Upstream & downstream products
Upstream raw materials
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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